It's fair to think that Kobo could do more on this front, but from a business standpoint it's difficult to fathom how syncing customer's side loaded content could be anything but burdensome and consumptive of unpaid resources.
It would be a great feature if left to the customer to decide whether they want particular books synced to/from their device on an individual basis. Obviously, each device would have to control whether each of its titles would be available to the other devices for syncing, but I guess this could be accomplished with a simple check box on each title in the library:books display pages. It would seem that requiring the user to allow the syncing by selecting a check box might be sufficient in terms of satisfying any privacy concerns, but no doubt it would also require a disclaimer screen of some sort to be displayed and agreed to, at least once, possibly every time?
The thing about wirelessly syncing bookmarks, etc, across devices is that one must sync the current device prior to switching and the new device prior to reading. Not exactly truly convenient on low powered devices that are often disconnected from the network like readers...
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